Methoxy-substituted TQEN family of fluorescent zinc sensors.

Two methoxy-substituted TQEN (N,N,N',N'-tetrakis(2-quinolylmethyl)ethylenediamine) derivatives, T(MQ)EN (N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine) and T(TMQ)EN (N,N,N',N'-tetrakis(5,6,7-trimethoxy-2-quinolylmethyl)ethylenediamine), have been prepared, and their fluorescence properties with respect to Zn2+ coordination were investigated. Introduction of a methoxy substituent at 6-position of the quinoline ring enhances the fluorescence intensity by 10-fold, and the three methoxy substituents in the 5,6,7-positions afford significant enhancement of the long-wavelength component of the fluorescence of zinc complex. The substituents did not alter the binding affinity of these compounds toward zinc ion significantly. T(MQ)EN was proved to be effective in detection of zinc ion in cells by fluorescent microscopy.